Born in Los Angeles, CA, Caan was the son of veteran film actor James Caan and former model-actress Sheila Ryan. His parents split up a year after his birth, but maintained a very active presence in his upbringing. His father took a hiatus from acting for several years in the 1980s to concentrate on coaching the younger Caan's Little League team. At the start of the 1990s, Caan drifted from school to school, spending time at the celebrity-magnet Beverly Hills High School before graduating from Excelsior High. Despite his perpetual love of baseball, Caan's hopes of having a professional career as a major leaguer lessened. He had designs on the music business, having formed a rap duo with his friend, the popular beat maker The Alchemist, called The Whooliganz, for which he and The Alchemist went by Mad Skillz and Mudfoot. The Whooliganz canvassed the L.A. rap scene and ended up out on tour with the likes of House of Pain and Cypress Hill, with the duo signing with credible rap hitmakers Tommy Boy Records. But after recording and releasing one single, "Put Your Handz Up," they saw their debut album, Make Way for the W shelved in 1994. At the end of high school, Caan went on tour as a roadie for Cypress Hill. But at the urging of his mother, he began training in the intensive program of the North Hollywood-based Playhouse West, where she was a frequent performer. His father soon tapped him for the title part of the film drama, "A Boy Called Hate" (1995), after which he began landing parts in independent films like Gregg Araki's surreal L.A.-based drama, "Nowhere" (1997). After a small turn in the pot comedy "Bongwater" (1998) opposite Luke Wilson, Caan took a step up with a studio film credit after he was cast as a hitman helping hunt down Will Smith in the Jerry Bruckheimer-Tony Scott paranoid thriller, "Enemy of the State" (1998). A year later, in the machismo-laden high school football drama, "Varsity Blues" (1999), Caan shed his performing inhibitions by appearing in only a cowboy hat, matching the actresses who were supposed to appear in a similar fashion. Caan's roles began to reflect his forthright sensibility, putting those qualities to maximum effect as a young hotshot broker in "Boiler Room" (2000) and a rabid professional wrestling fanatic in the Warner Brothers comedy "Ready to Rumble" (2000). The up-and-coming Caan reunited with Jerry Bruckheimer, tackling grand theft auto as a fast-driving car thief named Tumbler in the misfire, "Gone in Sixty Seconds" (2000). He next landed a part in "American Outlaws" (2001), a youth-oriented telling of the Jesse James-Cole Younger gang, with Caan donning another cowboy hat to play the brash outlaw, Cole Younger. Still, it was his quiet, controlled nature of the performance in "Boiler Room" that attracted writer-director David Atkins, who cast him as Helena Bonham Carter's menacing brother in the indie thriller "Novocaine" (2001), taking Caan into the world of drugs, sexual intrigue and seedy blackmail. While director Steven Soderbergh's Rat Pack update, "Ocean's Eleven" (2001), was in development in early 2001, with Caan cast as the wisecracking getaway driver Turk Malloy, the actor was tinkering with a small play which sprung from a year-plus romantic relationship. In the summer of 2001, after "Ocean's" wrapped and awaited its eventually successful fall release, Caan returned to Playhouse West to help mount the play, "Almost Love," a musing on the nature of post-collegiate age love which ran for a week of performances.By 2002, his "Gone in Sixty Seconds" co-star Nicolas Cage had recruited him for his directorial debut, "Sonny" (2002), as a former army soldier attempting to recruit the film's titular gigolo (James Franco) into a more legitimate life. Having soaked in the process of some top directors, Caan decided to have a go at directing and writing himself, churning out "Dallas 362" (2003), a carefully constructed retro tale of two Los Angeles friends (Caan and Shawn Hatosy) who drink and fight their way across the seedy underbelly of Los Angeles, only to find themselves torn apart when one tries to pull himself together and the other delves deeper into a life of crime. Following a reunion with the Ocean's gang for a crooked European vacation in "Ocean's Twelve" (2004), Caan balanced himself nicely between bigger films and somewhat smaller ones, spitting tart-tongued one-liners as an amoral attorney in the big-budget action thriller "Into the Blue" (2005) while casually charming and eventually degrading Jennifer Aniston's educated maid character in the independent comedy of manners, "Friends with Money" (2006). Caan returned to the director's chair with his scripted comedy "The Dog Problem" (2006), a low-key ensemble effort about romantically intertwined dog owners in Los Angeles. He turned to the right side of the law as a detective in the 1930s crime caper "Lonely Hearts" (2006), before Vegas beckoned again, and Turk Malloy was called back for heist duty in the summer smash, "Ocean's Thirteen" (2007). After a small and thankfully overlooked role in the much-maligned Eddie Murphy comedy "Meet Dave" (2008), Caan turned to the small screen with a recurring role on "Entourage" (HBO, 2004-11), playing an arrogant talent manager who gets under Eric's (Kevin Connolly) skin. While popping in and out of that series over its last remaining seasons, the actor wrote and starred in the indie drama, "Mercy" (2009), a self-therapeutic drama in which he played a cynical, but successful writer of young romance novels who falls for one of his critics (Wendy Glenn) despite not actually believing in love. Back on the small screen, Caan joined the cast of the updated "Hawaii 5-0" (CBS, 2010-), playing Detective Danny "Danno" Williams opposite Alex O'Loughlin and Grace Park. Caan's performance as the iconic "Book 'em, Danno" character received the majority of the buzz, with rumors of rampant scene-stealing by the young actor taking place in the first few episodes; all of which bode well for the anticipated series. While the show became a solid ratings winner for the network, Caan earned his due with a Best Supporting Actor nomination at the Golden Globes.